How to Ask a Woman on a Date - Cool Dating Advice

How to Ask a Woman on a Date

How to ask a woman on a date

You really like someone or you meet a person out on the town that you really connect with. The question is how do you ask a woman on a date? There is no magic bullet. You need to overcome your fear and follow through with asking her to meet out for coffee or dinner.

Men are afraid of rejection so they do not even ask and walk away. They are wishing they had the courage to talk to the woman that caught their eye.


You may meet someone interesting when grocery shopping, out with friends or maybe at work.

The last thing you want to do is meet a woman that you could connect with and look like you just rolled out of bed.


Wearing sweatpants and an old smelly t-shirt will not turn heads from the opposite sex.

You are not going to be dressed up nice to go to home depot or to jog 5 miles. When you do go out make sure you look well-groomed and dressed appropriately.

If you do meet a woman that you are interested in then you will look the part.

Confidence when talking

It is hard to go up to a stranger you see at a restaurant or bar and just go up to talk to them.

If you do notice someone that you would like to talk with then the best way to break the ice is to have someone introduce you to her.

Maybe you are at a dinner party with friends and one of them knows the woman you want to meet. You can easily have them introduce you to her.

There are many ways to meet a woman that men have used throughout time. The old buy them a drink so they will like you is an old one but not one I would use.

My sister said women do it all the time to get free drinks so how do you know if they are interested in you or are just using you for drinks.

When you do decide to meet a woman that has caught your interest be confident when approaching. You need to show confidence and look them straight in the eye when talking.

If your funny try breaking the ice with some comedic approach. Women love it when someone can make them laugh.

Imagine she will say yes to you

It is always good to visualize what you want to do and the outcome. This helps with confidence plus prepares you for the moment.


When you are getting up the nerve to ask out a woman imagine the outcome you want.

Athletes do this all the time before they go out to play. You can do it too but instead of sports, you are doing it to meet a woman.

Invite her do not ask a question

You do not want to say something like: “Do you want to…How about..etc.” You should be like let’s grab a coffee tomorrow at noon. This will show you have confidence and take initiative.

Many women like a decisive strong man to go out with and have fun with.

Do not come across arrogant or too cocky because that would be a turn-off.  This is the balance you have to find being confident but not an asshole.

Many men struggle with this because they are too arrogant and full of themselves.

Connect with her

If you meet someone for the first time and there is a little or a lot of synergy between you both. Keep the conversation going and really connect with her before you ask her out.

Men will sometimes just go up to a pretty woman in a bar or nightclub and just ask for their number. If you get her number I guarantee it’s not the right phone number.

That is the wrong way to approach a woman you are attracted to. You need to connect before setting up the next meeting with her.

You do this by working to get an introduction or reason to talk to her. Once you have an in then you need to ask questions to get her talking.

She starts talking and you seem interested then you should be good at getting a number.


The first connection should start with a conversation about her and not about you.

People want to talk about themselves they do not want to hear about your life at least to start.

Don’t talk about old girlfriends, old dates, your boring job, or your bad family. You should also not start talking about the weather or maybe your zodiac sign.

You need to let her talk and you need to listen to what she is saying.

The more you remember the more impressed she will be later on if you start seeing each other.

Ask a bunch of questions to get to know your date better. We have some really funny questions on another one of your posts.

Drinking to squash fear

If you are out drinking with friends that is ok but do not get too drunk. The problem is if you are too drunk it will be much harder to ask a woman out or communicate in a way that she would want to see you again.

You do not need the liquid courage to ask a woman out for coffee. It’s just a cup of coffee or lunch together no real big deal.

She says yes

You were introduced to a woman you find attractive. You have listened to her talk about her life and her interests.

You both feel a connection so you decide at the end of the night to ask her to catch lunch with you next week. She says yes but make sure you contain your excitement and just play it cool.

Don’t say something stupid like “Awesome you are so hot I did not think you would say yes.” This is the wrong response after you get a yes.

You need to say, “Sounds great see you tomorrow at Starbucks at 11:30 AM.”

You then need to just walk away and meet up at the time and date.

Fear is the mind-killer and date killer

Sometimes you have to face the fear of rejection. Who cares if you get rejected when you ask a woman out.

Nothing will happen to you but if you never ask a woman out you like she may be the one and you missed out on the perfect wife.

Life is too short to not take chances so make sure you take a chance every once in a while. The outcome of that chance may surprise you.


You need to put yourself out there in a position that might not be comfortable.

Life is short so you need to be bold. If you are single the next time you are out with friends just g up and talk to an attractive woman.

You have nothing to lose and it will open you up. You will be having fun and enjoying life with your friends and possibly a woman if you do what we recommend.

You may also like: How to Approach a Woman in a Bar

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